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In 2018, Routledge Press (New York and London) published Montgomery's second book "Smartphone Video Storytelling" as a hybrid textbook that includes a rich library of e-learning materials.

In 2015 he launched the Smart Film School as an online video academy to deliver training course packs for educators. The school includes more than 450 video tutorials organized into masterclasses that professors and students use to learn mobile journalism, mobile filmmaking and innovation methods.

Montgomery is the author of “Smartphone Video Storytelling” (Routledge Press: Taylor & Francis Group — 2018).

Montgomery published his first book on mobile journalism in 2014 - "A Field Guide for Mobile Journalism."

In 2011 he developed the mobile journalism training, technology and workflows used by hundreds of Radio Free Europe (RFE/RL) reporters and correspondents in 23 countries.

in 2011 he pioneered the mobile journalism strategy, training and workflows for Radio Free Europe - the first international broadcaster to train their entire staff in mobile journalism methods and also to outfit journalists with a custom mobile reporting app that Montgomery designed.

Montgomery redesigned the business section for The San Jose Mercury News in early 2007.

Montgomery has trained more than 20,000 people in mobile journalism methods including the United Nations, CNN, The New York Times and the Danish School of Journalism. in Since 2007 he has worked with USAID-funded Media Development projects in Egypt and Georgia and developed and produced multimedia training, mobile and digital journalism workshops in more than 22 countries.

In 2005, he retired from the Chicago Sun-Times to launch a consulting business and begin teaching visual journalism methods with media development projects worldwide.

Since leaving the Chicago Sun-Times in 2005, Montgomery has worked as a journalism educator for U.S. and foreign media groups including the Thomson Reuters Foundation, WAN-IFRA, Egypt Media Development Group, Pennsylvania Newspaper Association, IFRA, and INMA.

Working as the group's CEO, Montgomery incorporated the Visual Editors social network in 2004 as a 501(c)(3) non-profit charity, positioning the site as an educational exchange for student and professional journalists working in the world's newsrooms. The charity is operated by a volunteer board of directors.

As a visual editor, he led the 2003 redesign of the Chicago Sun-Times and the 2005 redesign of The San Francisco Examiner. In 2004, he founded Visual Editors, a non-profit that connects and provides educational resources for visual journalists worldwide. In 2005, he redesigned The Examiner newspaper for the San Francisco, Washington, D.C. and Baltimore metro markets.

Since 2003 he has been hired as a distinguished visiting professor to develop and teach journalism courses at the Medill School of Journalism, Northwestern University, Cairo University, EFJ School of new journalism in Paris, FH Wien School of journalism, the Danish School of Journalism and Stockholm University.

Montgomery worked as a newspaper editor and designer from 1990 to 2005 and was a principal editor and the designer of Chicago's Red Streak newspaper that was published by the Chicago Sun-Times starting in October, 2002 as a competitor to the Chicago Tribune's RedEye tabloid.

Montgomery was born in Naperville, Illinois in 1964 and currently resides in Berlin, Germany. He began his career as a graphics journalist at the Fort Lauderdale Sun-Sentinel in 1990 after graduating from Eastern Illinois University with a degree in journalism. He held a number of editorial positions for newspapers in Florida and Illinois between 1990 and 2005.